WO2004069891A1 - Composition polyol pour mousse de polyurethanne rigide et son procede de production - Google Patents

Composition polyol pour mousse de polyurethanne rigide et son procede de production Download PDF

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Publication number
WO2004069891A1
WO2004069891A1 PCT/JP2004/001196 JP2004001196W WO2004069891A1 WO 2004069891 A1 WO2004069891 A1 WO 2004069891A1 JP 2004001196 W JP2004001196 W JP 2004001196W WO 2004069891 A1 WO2004069891 A1 WO 2004069891A1
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WO
WIPO (PCT)
Prior art keywords
hfc
rigid polyurethane
polyurethane foam
polyol
composition
Prior art date
Application number
PCT/JP2004/001196
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English (en)
Japanese (ja)
Inventor
Natsuko Anraku
Masahiro Jinno
Fumio Shiroo
Hiroyuki Anzai
Takashi Shibanuma
Original Assignee
Toyo Tire & Rubber Co., Ltd.
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Publication date
Application filed by Toyo Tire & Rubber Co., Ltd. filed Critical Toyo Tire & Rubber Co., Ltd.
Publication of WO2004069891A1 publication Critical patent/WO2004069891A1/fr
Priority to HK06105579A priority Critical patent/HK1085494A1/xx

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
    • C08J9/143—Halogen containing compounds
    • C08J9/144—Halogen containing compounds containing carbon, halogen and hydrogen only
    • C08J9/146—Halogen containing compounds containing carbon, halogen and hydrogen only only fluorine as halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0025—Foam properties rigid
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes

Definitions

  • the present invention relates to a rigid polyurethane containing 1,1,1,1,3,3_pentafluoropropane (HFC-245fa) as an essential component of a foaming agent as a foaming agent component.
  • the present invention relates to a foam polyol composition and a method for producing a rigid polyurethane foam using HFC-245fa as a main component of a foaming agent. Background technology
  • HCFFC-14 lb 1,1-dichloro_1-fluorene (HCFC-14 lb), which has a low ozone layer rupture coefficient, is used as a foaming agent for rigid polyurethane foam, which is an excellent heat insulating material.
  • HCFFC-141b has a small ozone layer erosion coefficient but is not zero, and it has been decided that it will be abolished at the end of 2003 from the viewpoint of global environmental protection.
  • HCFC HFC
  • a low-boiling hydrocarbon such as n-pentane or low-mouth pentane
  • a low-boiling lauric hydrocarbon compound that does not contain chlorine is currently used as a blowing agent to replace 141b.
  • HFE with a smaller global warming coefficient— 254 pc are under consideration.
  • HFC—365 mfc has not been confirmed to be flammable according to the standards of the Japanese Fire Service Law, but the German standard has a flash point at 127 ° C, which is used as a blowing agent.
  • the polyol composition contained may be classified as a Class 4 Petroleum Class 1 Dangerous Goods specified by the Fire Service Law, and a polyol composition containing HCF C_141b as a blowing agent and a dangerous substance.
  • HFC-365mfc also has a problem that the compatibility with the polyol compound which is a main component of the polyol composition is poor.
  • HFE—254 pc is a foaming agent in the development stage, and has not been sufficiently studied. However, as a dangerous substance, it is close to HFC—365 mfc, and similar problems Having.
  • HFC-2445fa is a blowing agent that has no danger of ignition and does not need to be handled as a hazardous substance, but has a boiling point of 15 ° C and a vapor pressure at room temperature. Is high. Therefore, if HFC-245fa is used as a blowing agent, containers such as drums and petroleum cans containing the polyol composition may swell, especially in summer, and may be vulnerable to vaporization during opening. As a result, there arises a problem that the undiluted solution of the polyol composition is blown out and the content of the foaming agent is reduced by volatilization, and a foam having a predetermined density cannot be obtained. Disclosure of the invention
  • An object of the present invention is to provide a method for producing a rigid polyurethane foam, which is a polyol composition for a rigid polyurethane foam in which HFC-245fa is used as a foaming agent and whose vapor pressure is suppressed. Is to do.
  • the polyol composition for a rigid polyurethane foam of the present invention contains at least a polyol compound, a foaming agent, a foam stabilizer, and a catalyst, and is mixed with an isocyanate component containing a polyisocyanate compound to foam. Cured to form rigid polyurethane foam,
  • the object of the present invention can be achieved by using the polyol composition for a rigid polyurethane foam having the above configuration.
  • HFC-245fa is used as a foaming agent, and diethyleneglyconolemonoethyl ether acetate (hereinafter abbreviated as CAc (carbitol acetate)) is used as a vapor pressure reducing agent.
  • CAc diethyleneglyconolemonoethyl ether acetate
  • HFC-245fa / CAc weight ratio exceeds 955, the effect of lowering the vapor pressure will not be sufficiently exhibited, and the vapor pressure of the polyol composition for rigid polyurethane foam will increase.
  • the weight ratio of HFC-245fa / CAc is less than 60/40, the ratio of CAc becomes too large, and the physical properties of the foam may deteriorate.
  • Polyol compounds containing a tertiary amino group are more compatible with HFC-245fa than other polyol compounds, so a tertiary amino group-containing polyol compound is used in combination. As a result, a more excellent effect of lowering the vapor pressure of HFC-245fa can be obtained.
  • the reaction activity of the polyol composition is further increased, and the uniformity of the bubbles of the obtained rigid polyurethane foam is increased, and the adhesion to the face material is improved.
  • the effect of increasing the bonding strength is also obtained.
  • the nitrogen based on the tertiary amino group is less than 0.5 in the polyol compound, the effect of lowering the vapor pressure, the uniformity of the bubbles, and the adhesive strength with the face material are not sufficiently improved, and exceeds 9% by weight.
  • the dimensional stability of the resulting rigid polyurethane foam decreases.
  • the nitrogen based on the tertiary amino group is more preferably 1.5 to 8.5% by weight in the polyol compound.
  • the above polyol composition for rigid polyurethane foam is further used as a second blowing agent.
  • Containing 1,1,1,3,3—pentafluorobutane (HFC—365 mfc), HFC — 24fa / HFC — 365 mfc60Z40, HFC-245fa + HFC-365mfc) / CAc 955 to 640 (weight ratio) is preferable.
  • HFC—365mfc has good compatibility with HFC—245ia, and HFC—2
  • HFC_365mfc it is a compound with a higher boiling point (40. 2.C) than 45fa.
  • HFC_365mfc By using HFC_365mfc together, it can improve the foaming properties and the physical properties of the obtained rigid polyurethane foam.
  • the vapor pressure of HFC-245fa can be further suppressed while maintaining the same.
  • the weight ratio of HFC-245fa / HFC-365mfc is less than 60/40, the content of HFC_365mfc increases, resulting in a lower flash point and higher polio.
  • the composition may be recognized as a highly flammable petroleum among the Class 4 dangerous goods. If the weight ratio of (HFC-245fa + HFC-365mfc) / CAc exceeds 95/5, the ratio of CAc becomes too small, and the effect of the addition cannot be sufficiently exhibited. If the weight ratio is less than 60/40, the proportion of CA c becomes too large, and the physical properties of the foam may deteriorate.
  • the ZCAc weight ratio is more preferably from 93/7 to 70/30.
  • HFE-254 pc methoxetane tetrafluoride
  • HFC-245fa / HFE-254pc is less than 50/50, the content of HFE-254pc increases, resulting in a lower flash point and lower polyol composition.
  • the dangerous goods of Class 4 there are cases where it is recognized as highly flammable petroleum. If the weight ratio of (HFC-245fa + HFE-254pc) / CAc exceeds 955, the ratio of CAc becomes too small, and the effect of its addition cannot be sufficiently exhibited. If the weight ratio is less than 60 to 40, the ratio of CA c becomes too large, and the physical properties of the form may deteriorate.
  • the CAc may be premixed with HFC-245ia, and HFC-365mfc or HFE-254pc and mixed with the polyol compound as a foaming agent composition. May be separately added and mixed, and as long as they coexist in the polyol composition, the order of addition and form are not limited.
  • C Ac as a component of the polyol composition also improved the adhesive strength between the rigid polyurethane foam and the face material.
  • HFC-245fa or HFC-245fa and HFC-365mfc or HFE-254pc is used as the blowing agent, the blowing agent
  • the temperature of the contact surface decreases when the foaming stock solution obtained by mixing the isocyanate component and the polyol composition comes into contact with the face material, etc., because the compatibility between the polyol component and the polyol component is not good.
  • HFC-245-fa blooms before the curing reaction starts, and then a foaming reaction occurs, resulting in the foam cells near the interface becoming rough, resulting in reduced adhesiveness to the surface material.
  • CAc has an effect of improving the compatibility between HFC-245fa and the polyol compound, and thus improves the adhesive strength between the rigid polyurethane foam and the face material.
  • Another aspect of the present invention is a method for producing a rigid polyurethane foam by mixing an isocyanate component and a polyol composition, foaming and curing the mixture to obtain a rigid polyurethane foam. It is characterized by using the polyol composition for rigid polyurethane foam according to any one of claims 1 to 3.
  • the polyol composition for hard polyurethane of the present invention contains at least a polyol compound, a foam stabilizer, and a catalyst in addition to the foaming agent.
  • the polyol compound contains a tertiary amino group-containing polyol compound.
  • polyol compound known polyol compounds for rigid polyurethane foam can be used without limitation.
  • polyol compounds include tertiary amino group-containing polyol compounds, aliphatic polyols, aromatic polyols, and the like.
  • the tertiary amino group-containing polyol compound is obtained by using a primary or secondary amine as an initiator, such as an alkylene oxide, specifically, propylene oxide (PO) or ethylenoxide (EO).
  • PO propylene oxide
  • EO ethylenoxide
  • polyfunctional polyol compounds obtained by ring-opening addition polymerization of at least one of styrene oxide (SO), tetrahydrofuran and the like.
  • Examples of the primary or secondary amine initiator which is an initiator for the tertiary amino group-containing polyol compound include aliphatic primary and secondary amines such as ammonia, methylamine, and ethylamine.
  • Aliphatic polyols include alkylene oxides, specifically propylene oxide (P 0), ethylene oxide (EO), and alkylene oxides as aliphatic or alicyclic polyfunctional active hydrogen compounds as polyol initiators. It is a polyfunctional oligomer obtained by ring-opening addition polymerization of one or more cyclic ethers such as styrene oxide (SO) and tetrahydrofuran.
  • polyol initiator of the aliphatic polyol examples include ethylene glycol, propylene glycol, 1,4-butanediol, 1,3-butanediol, 1,6-hexanediol, and neopentyl glycol.
  • triols such as trimethylolpropane and glycerin, tetrafunctional alcohols such as pentaerythritol, polyhydric alcohols such as sorbitol and sucrose, and water. It is.
  • the aromatic polyol is a polyol compound obtained by the above-described method of adding an alkylene oxide to a polyfunctional active hydrogen compound having an aromatic ring in the molecule, or an ester of an aromatic polycarboxylic acid and a polyhydric alcohol. Examples thereof include polyol compounds.
  • polyol compounds obtained by adding the above-described alkylene oxide to a polyfunctional active hydrogen compound at least one of PO, E ⁇ , and SO is opened to hydroquinone, bisphenol A, and the like. Cycloadded compounds are specifically exemplified.
  • ester of an aromatic polycarboxylic acid and a polyhydric alcohol include ester polyols at the terminal of a hydroxyl group of terephthalic acid, phthalic acid, isophthalic acid, etc., and ethylene daryl, diethylene glycol, etc.
  • the above polyol compound preferably has a hydroxyl value of from 200 to 600 mg KOH / g.
  • a tertiary amino group-containing polyol compound or an aliphatic polyol is used among these polyol compounds, an effect of lowering the viscosity of the polyol composition can be obtained.
  • a known catalyst for rigid polyurethane foam can be used without limitation.
  • triethylenediamine, N-methylmorpholine, N, N, N ', N'-tetramethylethylenediamine, N, N, N ,, N'-tetramethylhexamethylenediamine And tertiary amines such as DBU, DBU, and the like
  • metal-based catalysts such as dibutyltin dilaurate, dibutyltin diacetate, and tin octylate are exemplified as the urethanization reaction catalyst.
  • the rigid polyurethane foam means that the isocyanate group forming the polymer may have only a urethane bond, and may have a rare bond or an isocyanurate bond.
  • a catalyst that forms an isocyanurate bond that contributes to improving the flame retardancy in the structure of the polyurethane molecule.
  • a catalyst that forms an isocyanurate bond that contributes to improving the flame retardancy in the structure of the polyurethane molecule.
  • potassium acetate and potassium octylate are preferred.
  • Some of the above tertiary amine catalysts also promote the isocyanurate ring formation reaction.
  • a catalyst that promotes the formation of isocyanurate bonds and a catalyst that promotes the formation of urethane bonds may be used in combination.
  • foam stabilizer a known foam stabilizer for rigid polyurethane foam can be used without limitation.
  • foam stabilizer polydimethylsiloxane and a graft copolymer or a block copolymer of polydimethylsiloxane and polyalkylene oxide are generally used.
  • polyalkylene oxide include polyethylene oxide and polypropylene oxide having an average molecular weight of 500 to 800, and a random copolymer or block of ethylene oxide and propylene oxide. A copolymer is used.
  • a flame retardant in the polyol composition for rigid polyurethane foam of the present invention, a flame retardant, a colorant, an antioxidant, an anti-scorch agent and the like well known to those skilled in the art can be used.
  • Examples of the flame retardant include metal compounds such as halogen-containing compounds, organic phosphoric esters, antimony trioxide, and aluminum hydroxide.
  • these flame retardants for example, when an organic phosphoric acid ester is added in excess, the physical properties of the obtained rigid polyurethane foam may be reduced, and metal compound powders such as antimony trioxide may be used. Excessive addition may cause problems such as affecting the foaming behavior of the foam, and the amount of addition is limited to a range that does not cause such problems.
  • a plasticizer in the rigid polyurethane foam of the present invention, if necessary. It is preferable that such a plasticizer also contributes to flame retardancy.
  • halogenated alkyl esters of phosphoric acid, alkyl phosphoric acid esters, aryl phosphoric acid esters, and phosphonic acid esters can be used.
  • Tris (2-chloroethyl) phosphate CLP, Daihachi Chemical
  • Tris (/ 3-cloguchi propyl) phosphate TCPP, Daihachi Chemical
  • Trib Tokishe Examples include tyl phosphate (TBXP, manufactured by Daihachi Chemical), triptyl phosphate, triethyl phosphate, creatinyl phosphate, dimethyl methyl phosphonate, etc., and one or more of these can be used. It is.
  • the added amount of the plasticizer is preferably 5 to 30 parts by weight based on 100 parts by weight of the polyol component. Beyond this range, plasticization In some cases, problems such as insufficient effect or deterioration of the physical properties of the foam may occur.
  • a polyisocyanate compound that forms a rigid polyurethane foam when mixed and reacted with a polyol composition it is excellent in ease of handling, reaction speed, and physical properties of the resulting rigid polyurethane foam.
  • Use liquid MDI because of its low cost.
  • the liquid MDI include crude (crude) MDI (c-MDI) (44 V-10, 44 V—20, etc. (manufactured by Sumitomo Pier Urethane Co., Ltd.)), and MDI containing urethane imine ( Millionate MTL; manufactured by Japan Polyurethane Industry Co., Ltd.).
  • the rigid (polyurethane) foams to be formed have excellent physical properties such as mechanical strength and are inexpensive. Use is particularly preferred.
  • another polyisocyanate compound may be used in combination.
  • a polyisocyanate compound a di- or poly-isocyanate compound known in the field of polyurethane can be used without limitation.
  • the polyol composition for a rigid polyurethane foam of the present invention can be used for the production of a rigid polyurethane foam that is continuously produced, such as a slab stock foam, a sandwich panel, a rigid polyurethane foam sandwich panel that is injection-molded, and a spray foam. It is.
  • the constituent materials of the polyol composition are shown in Table 1.
  • the composition of the polyol composition and the amount (parts by weight) of the foaming agent composition are described in Tables 2 to 4.
  • the amount of the foaming agent composition was adjusted so that the density of the rigid polyurethane foam at the time of free foaming was 25 kg / m 3 .
  • the blowing agent composition contains carbitol acetate (HFC-245ia, HFC-365mfc, HFE-254pc), an additive that reduces the vapor pressure of the blowing agent. CA c) is added in advance.
  • the rigid polyurethane foam was produced by a conventional method. That is, in the compositions shown in Table 1, components other than the isocyanate component and the foaming agent composition were mixed and stirred to adjust the polyol composition, the temperature was adjusted to 20 ° C, and then 20 ° C. The polyol component and the isocyanate component, the temperature of which was adjusted to C, were mixed and stirred at a predetermined ratio, and were foam-cured to obtain a rigid polyurethane foam.
  • a 50 mm x 50 mm x 5 O mm cube was cut out from the foam that was freely foamed in the container, and measured according to JIS 951 (foamed plastic insulation material).
  • the foam that was freely foamed in the container was visually observed.
  • the evaluation results are shown according to the following criteria.
  • ⁇ The cells are uniform and fine, and are equivalent to HCFC-141b foam.
  • ⁇ Cell roughening, slightly inferior to HCFC-141b foam.
  • the evaluation results are shown in the lower part of Tables 2 to 4.
  • the blowing agent composition shown in Table 2 is a composition in which HFC-245fa and CAc which is a vapor pressure reducing agent are mixed in advance
  • the blowing agent composition shown in Table 3 is HFC-2 45 fa, HFC-365 mfc and three components of CAc
  • the blowing agent composition shown in Table 4 was obtained by mixing HFC-245fa, HFE-254pc and CAc in advance. It is a composition consisting of three components. From the results in these tables, it can be seen that the foaming agent composition of the present invention significantly reduces the vapor pressure of the foaming agent, and is handled in the same manner as the conventional polyol composition using HCFC-141b.
  • HFC- 2 4 5 fa ZH FE _ 2 5 4 pc is In the case of 400 (Comparative Example 7), the amount of HFC-365 mic or HFE-254 pc added was too large. The dimensional stability was that HCFC-141 was used as the blowing agent. It is lower than the completed form.
  • a polyester composition for rigid polyurethane foam which uses HFC-245fa as a foaming agent and suppresses its vapor pressure is extremely low.
  • a method for producing a rigid polyurethane foam can be provided. Therefore, the industrial significance of the present invention is great.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne une composition de polyol pour mousses de polyuréthanne rigides, que l'on utilise en combinaison avec HFC-245fa, tenant lieu d'agent gonflant à une pression de vapeur réduite de l'agent gonflant. L'ingrédient de l'agent gonflant renferme 1,1,1,3,3-pentafluoropropane (HFC-245fa). La composition renferme un acétate d'éther monoéthyle glycol diéthylène et un ou plusieurs composés polyol comprenant un composé polyol ayant un groupe amino tertiaire, le contenu des atomes d'azote pouvant être attribué à l'amino tertiaire étant compris entre 0,5 et 9 % en poids d'après les composés polyol. L'utilisation de l'ingrédient de l'agent gonflant qui comporte en outre HFC-365mfc ou HFE-254pc est utilisé de préférence.
PCT/JP2004/001196 2003-02-06 2004-02-05 Composition polyol pour mousse de polyurethanne rigide et son procede de production WO2004069891A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
HK06105579A HK1085494A1 (en) 2003-02-06 2006-05-15 Polyol composition for rigid polyurethane foam andprocess for producing rigid polyurethane foam

Applications Claiming Priority (2)

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JP2003029407A JP3902143B2 (ja) 2003-02-06 2003-02-06 硬質ポリウレタンフォーム用ポリオール組成物及び硬質ポリウレタンフォームの製造方法
JP2003-29407 2003-02-06

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KR (1) KR100982430B1 (fr)
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HK (1) HK1085494A1 (fr)
TW (1) TW200418897A (fr)
WO (1) WO2004069891A1 (fr)

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CN102604022A (zh) * 2012-03-08 2012-07-25 巨化集团公司 一种制冷行业用硬质聚氨酯泡沫多元醇组合物
JP6764664B2 (ja) * 2016-02-29 2020-10-07 三洋化成工業株式会社 （ポリオキシアルキレン）ポリオールの製造方法および硬質ポリウレタンフォームの製造方法
CN109438664B (zh) * 2018-09-30 2021-06-18 山东一诺威新材料有限公司 家电用阻燃性硬泡聚氨酯材料及其制备方法
KR102140285B1 (ko) * 2018-12-07 2020-07-31 서울시립대학교 산학협력단 폴리우레탄 폼 성형체 및 폴리우레탄 폼 제조방법

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TWI332959B (fr) 2010-11-11
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CN1747978A (zh) 2006-03-15
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